Triethylamine → HCID 3510845, compound

HRID 1440816Notes

Reaction equation

HRID 1440816 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Br:2][CH2:3][CH2:4][NH:5][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][C:7]([F:6])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 3510845HCID 3510845, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Conditions

Temperature
5 °C

Procedure

To a suspension containing 0.23 mol of-bromoethylamine hydrobromide in 200 ml of chloroform, stirred at 5° C., is added dropwise a solution containing 0.21 mol of 4-fluorobenzoyl chloride in 50 ml of chloroform, followed by a solution containing 0.46 mol of triethylamine in 100 ml of chloroform. The mixture is then stirred at room temperature for 1 hour and then at reflux for 4 hours. After cooling and evaporation of the solvent, the residue is taken up in 200 ml of ether. After filtration of the salts and concentration of the solvent, the expected product is obtained by purification of the residue by chromatography on a column of silica, using a dichloromethane/acetone (98/2) mixture as eluent.

Workup

  1. additionis added dropwise a solution
  2. stirringThe mixture is then stirred at room temperature for 1 hour
  3. temperatureat reflux for 4 hours
  4. temperatureAfter cooling
  5. customevaporation of the solvent
  6. filtrationAfter filtration of the salts and concentration of the solvent

Sources & evidence

ORD record
ord-5eb81d0f7aef4447ab890af40d7bb8f1
Source dataset
uspto-grants-1996_03
Patent number
US05500443

Reaction notes

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